Sodium Carbonate → 5-Amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide

HRID 2244452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244452
C(OC(=O)[NH:7][C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[C:14](=[O:23])[NH:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[CH:17]=1)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O>[CH3:22][C:18]1[CH:17]=[C:16]([NH:15][C:14]([C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[NH2:7])=[O:23])[CH:21]=[CH:20][N:19]=1

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 68406749Carbamic acid, [2-methyl-4-[[(2-methyl-4-pyridinyl)amino]carbonyl]-5-thiazolyl]-, 1,1-dimethylethyl ester

Produkt 1

HCID 866065745-Amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

[2-Methyl-4-(2-methyl-pyridin-4-ylcarbamoyl)-thiazol-5-yl]-carbamic acid tert-butyl ester (0.532 g, 1.53 mmol) was dissolved in 12 mL trifluoroacetic acid and stirred at room temperature for 30 min. The reaction mixture was treated with 2N sodium carbonate solution until pH 10 and extracted three times with ethyl acetate (50 mL each). The organic phases were pooled, dried with sodium sulfate and evaporated. The crude product was flash-chromatographed on silica gel with heptane/ethyl acetate 100:0→0:100 gradient to yield 5-amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide as a light yellow solid (0.361 g, 95%), MS (ISP): m/e=249.1 (M+H+).

Aufarbeitung

  1. extractionextracted three times with ethyl acetate (50 mL each)
  2. dry with materialdried with sodium sulfate
  3. customevaporated
  4. customThe crude product was flash-chromatographed on silica gel with heptane/ethyl acetate 100:0→0:100 gradient

Quellen und Nachweise

ORD-Eintrag
ord-252f79b22d034575b5a00c6f38ca94ef
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678815B2

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